Hypolipidemic agent Z-guggulsterone: Metabolism interplays with induction of carboxylesterase and bile salt export pump

Journal of Lipid Research

Volumn 53, Issue 3, 2012, Pages 529-539

  Yang, Dongfang ^a   Yang, Jian ^a   Shi, Deshi ^a   Xiao, Da ^a   Chen, Yi Tzai ^a   Black, Chris ^b   Deng, Ruitang ^a   Yan, Bingfang ^a  

^a UNIVERSITY OF RHODE ISLAND   (United States)

^b IntelliCyt Corporation   (United States)

Author keywords

Antioxidant; Atherlosclerosis; Bile acids; Carboxylesterase; Cytochrome P450 7A1; Dyslipidemias; Transactivation

Indexed keywords

BILE SALT; BILE SALT EXPORT PUMP; CARBOXYLESTERASE; CHOLESTEROL 7ALPHA MONOOXYGENASE; CHOLESTEROL ESTERASE; CYTOCHROME P450 3A4; DRUG METABOLITE; GUGGULSTERONE; PHYTOSTEROL; UNCLASSIFIED DRUG; VERY LOW DENSITY LIPOPROTEIN CHOLESTEROL; Z GUGGULSTERONE;

ARTICLE; CHOLESTEROL METABOLISM; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG EFFICACY; DRUG MECHANISM; DRUG METABOLISM; DRUG POTENCY; DRUG PROTEIN BINDING; DRUG STRUCTURE; DRUG TARGETING; ENZYME ACTIVATION; ENZYME METABOLISM; HUMAN; HUMAN CELL; LIPOLYSIS; PRIORITY JOURNAL; PROTEIN EXPRESSION;

ANIMALS; ATP-BINDING CASSETTE TRANSPORTERS; CARBOXYLIC ESTER HYDROLASES; CELLS, CULTURED; CHOLESTEROL 7-ALPHA-HYDROXYLASE; CYTOCHROME P-450 CYP3A; HEPATOCYTES; HYPOLIPIDEMIC AGENTS; MALE; MICE; PREGNENEDIONES; PROMOTER REGIONS, GENETIC; REVERSE TRANSCRIPTASE POLYMERASE CHAIN REACTION;

EID: 84863229181     PISSN: 00222275     EISSN: 15397262     Source Type: Journal    
DOI: 10.1194/jlr.M014688     Document Type: Article

References (37)

1. Buemi, M., C. Aloisi, F. Fulvio, C. Caccamo, E. Cavallaro, E. Crascì, M. Criseo, F. Corica, and N. Frisina. 2005. Cardiorenal consequences of atherosclerosis and statins therapy: from the past to the future. Curr. Pharm. Des. 11:3973-3984. (Pubitemid 41632248)
2. Sundaram, M., and Z. Yao. 2010. Recent progress in understanding protein and lipid factors affecting hepatic VLDL assembly and secretion. Nutr. Metab. (Lond). 7:35.
3. Wei, E., M. Alam, F. Sun, L. B. Agellon, D. E. Vance, and R. Lehner. 2007. Apolipoprotein B and triacylglycerol secretion in human triacylglycerol hydrolase transgenic mice. J. Lipid Res. 48:2597-2606. (Pubitemid 350272844)
4. Wei, E., Y. Ben Ali, J. Lyon, H. Wang, R. Nelson, V. W. Dolinsky, J. R. Dyck, G. Mitchell, G. S. Korbutt, and R. Lehner. 2010. Loss of TGH/Ces3 in mice decreases blood lipids, improves glucose tolerance, and increases energy expenditure. Cell Metab. 11:183-193.
5. Blais, D. R., R. K. Lyn, M. A. Joyce, Y. Rouleau, R. Steenbergen, N. Barsby, L. F. Zhu, A. F. Pegoraro, A. Stolow, D. L. Tyrrell, et al. 2010. Activity-based protein profiling identifies a host enzyme, carboxylesterase 1, which is differentially active during hepatitis C virus replication. J. Biol. Chem. 285:25602-25612.
6. Zhao, B., R. Natarajan, and S. Ghosh. 2005. Human liver cholesteryl ester hydrolase: cloning, molecular characterization, and role in cellular cholesterol homeostasis. Physiol. Genomics. 23:304-310. (Pubitemid 44437966)
7. Chiang, J. Y. 2009. Bile acids: regulation of synthesis. J. Lipid Res. 50: 1955-1966.
8. Dawson, P. A., T. Lan, and A. Rao. 2009. Bile acid transporters. J. Lipid Res. 50:2340-2357.
9. Urizar, N. L., and D. D. Moore. 2003. GUGULIPID: a natural cholesterol- lowering agent. Annu. Rev. Nutr. 23:303-313. (Pubitemid 37059726)
10. Szapary, P. O., M. L. Wolfe, L. T. Bloedon, A. J. Cucchiara, A. H. DerMarderosian, M. D. Cirigliano, and D. J. Rader. 2003. Guggulipid for the treatment of hypercholesterolemia: a randomized controlled trial. JAMA. 290:765-772. (Pubitemid 37432953)
11. Nohr, L. A., L. B. Rasmussen, and J. Straand. 2009. Resin from the mukul myrrh tree, guggul, can it be used for treating hypercholesterolemia? A randomized, controlled study. Complement. Ther. Med. 17:16-22.
12. Deng, R., D. Yang, A. Radke, J. Yang, and B. Yan. 2007. The hypolipidemic agent guggulsterone regulates the expression of human bile salt export pump: dominance of transactivation over farsenoid X receptor-mediated antagonism. J. Pharmacol. Exp. Ther. 320: 1153-1162. (Pubitemid 46294057)
13. Gopal, K., R. K. Saran, S. Nityanand, P. P. Gupta, M. Hasan, S. K. Das, N. Sinha, and S. S. Agarwal. 1986. Clinical trial of ethyl acetate extract of gum gugulu (gugulipid) in primary hyperlipidemia. J. Assoc. Physicians India. 34:249-251.
14. Nityanand, S., J. S. Srivastava, and O. P. Asthana. 1989. Clinical trials with gugulipid. A new hypolipidaemic agent. J. Assoc. Physicians India. 37:323-328.
15. Urizar, N. L., A. B. Liverman, D. T. Dodds, F. V. Silva, P. Ordentlich, Y. Yan, F. J. Gonzalez, R. A. Heyman, D. J. Mangelsdorf, and D. D. Moore. 2002. A natural product that lowers cholesterol as an antagonist ligand for FXR. Science. 296:1703-1706. (Pubitemid 34579172)
16. Yang, D., R. E. Pearce, X. Wang, R. Gaedigk, Y. J. Y. Wan, and B. Yan. 2009. Human carboxylesterases HCE1 and HCE2: ontogenic expression, inter-individual variability and differential hydrolysis of oseltamivir, aspirin, deltamethrin and permethrin. Biochem. Pharmacol. 77:238-247.
17. Fukami, T., M. Nakajima, T. Maruichi, S. Takahashi, M. Takamiya, Y. Aoki, H. L. McLeod, and T. Yokoi. 2008. Structure and characterization of human carboxylesterase 1A1, 1A2, and 1A3 genes. Pharmacogenet. Genomics. 18:911-920.
18. Shi, D., J. Yang, D. Yang, E. L. LeCluyse, C. Black, L. You, F. Akhlaghi, and B. Yan. 2006. Anti-influenza prodrug oseltamivir is activated by carboxylesterase human carboxylesterase 1, and the activation is inhibited by antiplatelet agent clopidogrel. J. Pharmacol. Exp. Ther. 319:1477-1484.
19. Shi, D., D. Yang, E. P. Prinssen, B. E. Davies, and B. Yan. 2011. Surge in expression of carboxylesterase 1 during the post-neonatal stage enables a rapid gain of the capacity to activate the anti-influenza prodrug oseltamivir. J. Infect. Dis. 203:937-942.
20. 50 shift approach facilitates kinact assay design. Xenobiotica. 39:99-112.
21. Shi, D., D. Yang, and B. Yan. 2010. Dexamethasone transcriptionally increases the expression of the pregnane X receptor and synergistically enhances pyrethroid esfenvalerate in the induction of cytochrome P450 3A23. Biochem. Pharmacol. 80:1274-1283.
22. Yang, D., Y. Li, X. Yuan, L. Matoney, and B. Yan. 2001. Regulation of rat carboxylesterase expression by 2,3,7,8-tetrachlorodibenzo- p - dioxin (TCDD): a dose-dependent decrease in mRNA levels but a biphasic change in protein levels and activity. Toxicol. Sci. 64: 20-27. (Pubitemid 33062184)
23. Liu, F., X. Song, D. Yang, R. Deng, and B. Yan. 2008. The far and distal enhancers in the CYP3A4 gene co-ordinate the proximal promoter in responding similarly to the pregnane X receptor but differentially to hepatocyte nuclear factor-4alpha. Biochem. J. 409:243-250.
24. Yang, D., J. Yang, D. Shi, R. Deng, and B. Yan. 2011. Scoparone potentiates transactivation of the bile salt export pump gene and this effect is enhanced by cytochrome P450 metabolism but abolished by a PKC inhibitor. Br. J. Pharmacol. 164:1547-1557.
25. Zhu, W., L. Song, H. Zhang, L. Matoney, E. LeCluyse, and B. Yan. 2000. Dexamethasone differentially regulates expression of carboxylesterase genes in humans and rats. Drug Metab. Dispos. 28: 186-191. (Pubitemid 30069003)
26. Cui, J., L. Huang, A. Zhao, J. L. Lew, J. Yu, S. Sahoo, P. T. Meinke, I. Royo, F. Pelaez, and S. D. Wright. 2003. Guggulsterone is a farnesoid X receptor antagonist in coactivator association assays but acts to enhance transcription of bile salt export pump. J. Biol. Chem. 278:10214-10220. (Pubitemid 36800282)
27. Ellis, E., M. Axelson, A. Abrahamsson, G. Eggertsen, A. Thörne, G. Nowak, B. G. Ericzon, I. Björkhem, and C. Einarsson. 2003. Feedback regulation of bile acid synthesis in primary human hepatocytes: evidence that CDCA is the strongest inhibitor. Hepatology . 38:930-938. (Pubitemid 37221676)
28. th edition. C. D. Klaassen, editor. McGraw-Hill, New York. 139-162.
29. Holmes, R. S., M. W. Wright, S. J. Laulederkind, L. A. Cox, M. Hosokawa, T. Imai, S. Ishibashi, R. Lehner, M. Miyazaki, E. J. Perkins, et al. 2010. Recommended nomenclature for five mammalian carboxylesterase gene families: human, mouse, and rat genes and proteins. Mamm. Genome. 21:427-441.
30. Ding, X., and J. L. Staudinger. 2005. The ratio of constitutive androstane receptor to pregnane X receptor determines the activity of guggulsterone against the Cyp2b10 promoter. J. Pharmacol. Exp. Ther. 314:120-127. (Pubitemid 41058248)
31. Ingelman-Sundberg, M., S. C. Sim, A. Gomez, and C. Rodriguez- Antona. 2007. Influence of cytochrome P450 polymorphisms on drug therapies: pharmacogenetic, pharmacoepigenetic and clinical aspects. Pharmacol. Ther. 116:496-526. (Pubitemid 350116943)
32. Keshava, C., E. C. McCanlies, and A. Weston. 2004. CYP3A4 polymorphisms-- potential risk factors for breast and prostate cancer: a HuGE review. Am. J. Epidemiol. 160:825-841. (Pubitemid 39434767)
33. Martínez-Jiménez, C. P., R. Jover, M. T. Donato, J. V. Castell, and M. J. Gómez-Lechón. 2007. Transcriptional regulation and expression of CYP3A4 in hepatocytes. Curr. Drug Metab. 8:185-194. (Pubitemid 46218685)
34. Yu, B. Z., R. Kaimal, S. Bai, K. A. El Sayed, S. A. Tatulian, R. J. Apitz, M. K. Jain, R. Deng, and O. G. Berg. 2009. Effect of guggulsterone and cembranoids of Commiphora mukul on pancreatic phospholipase A(2): role in hypocholesterolemia. J. Nat. Prod. 72:24-28.
35. Ellis, E. C. S. 2006. Suppression of bile acid synthesis by thyroid hormone in primary human hepatocytes. World J. Gastroenterol. 12: 4640-4645.
36. Xiang, X., Y. Han, M. Neuvonen, J. Laitila, P. J. Neuvonen, and M. Niemi. 2010. High performance liquid chromatography-tandem mass spectrometry for the determination of bile acid concentrations in human plasma. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 878:51-60.
37. Owsley, E., and J. Y. Chiang. 2003. Guggulsterone antagonizes farnesoid X receptor induction of bile salt export pump but activates pregnane X receptor to inhibit cholesterol 7alpha-hydroxylase gene. Biochem. Biophys. Res. Commun. 304:191-195. (Pubitemid 36434215)